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Journal articles on the topic 'Nucleotide sugars'

Author: Grafiati

Published: 4 June 2021

Last updated: 13 February 2022

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1

Mikkola, Satu. "Nucleotide Sugars in Chemistry and Biology." Molecules 25, no. 23 (December 6, 2020): 5755. http://dx.doi.org/10.3390/molecules25235755.

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Nucleotide sugars have essential roles in every living creature. They are the building blocks of the biosynthesis of carbohydrates and their conjugates. They are involved in processes that are targets for drug development, and their analogs are potential inhibitors of these processes. Drug development requires efficient methods for the synthesis of oligosaccharides and nucleotide sugar building blocks as well as of modified structures as potential inhibitors. It requires also understanding the details of biological and chemical processes as well as the reactivity and reactions under different conditions. This article addresses all these issues by giving a broad overview on nucleotide sugars in biological and chemical reactions. As the background for the topic, glycosylation reactions in mammalian and bacterial cells are briefly discussed. In the following sections, structures and biosynthetic routes for nucleotide sugars, as well as the mechanisms of action of nucleotide sugar-utilizing enzymes, are discussed. Chemical topics include the reactivity and chemical synthesis methods. Finally, the enzymatic in vitro synthesis of nucleotide sugars and the utilization of enzyme cascades in the synthesis of nucleotide sugars and oligosaccharides are briefly discussed.

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2

Figueroa, Carlos M., John E. Lunn, and Alberto A. Iglesias. "Nucleotide-sugar metabolism in plants: the legacy of Luis F. Leloir." Journal of Experimental Botany 72, no. 11 (May 5, 2021): 4053–67. http://dx.doi.org/10.1093/jxb/erab109.

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Abstract This review commemorates the 50th anniversary of the Nobel Prize in Chemistry awarded to Luis F. Leloir ‘for his discovery of sugar-nucleotides and their role in the biosynthesis of carbohydrates’. He and his co-workers discovered that activated forms of simple sugars, such as UDP-glucose and UDP-galactose, are essential intermediates in the interconversion of sugars. They elucidated the biosynthetic pathways for sucrose and starch, which are the major end-products of photosynthesis, and for trehalose. Trehalose 6-phosphate, the intermediate of trehalose biosynthesis that they discovered, is now a molecule of great interest due to its function as a sugar signalling metabolite that regulates many aspects of plant metabolism and development. The work of the Leloir group also opened the doors to an understanding of the biosynthesis of cellulose and other structural cell wall polysaccharides (hemicelluloses and pectins), and ascorbic acid (vitamin C). Nucleotide-sugars also serve as sugar donors for a myriad of glycosyltransferases that conjugate sugars to other molecules, including lipids, phytohormones, secondary metabolites, and proteins, thereby modifying their biological activity. In this review, we highlight the diversity of nucleotide-sugars and their functions in plants, in recognition of Leloir’s rich and enduring legacy to plant science.

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3

Velíšek, J., and K. Cejpek. "Biosynthesis of food constituents: Saccharides. 1. Monosaccharides, oligosaccharides, and related compounds – a review." Czech Journal of Food Sciences 23, No. 4 (November 15, 2011): 129–44. http://dx.doi.org/10.17221/3383-cjfs.

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This review article presents a survey of selected principal biosynthetic pathways that lead to the most important monosaccharides, oligosaccharides, sugar alcohols, and cyclitols in foods and in food raw materials and informs nonspecialist readers about new scientific advances as reported in recently published papers. Subdivision of the topics is predominantly via biosynthesis. Monosaccharides are subdivided to sugar phosphates, sugar nucleotides, nucleotide-glucose interconversion pathway sugars, nucleotide-mannose interconversion pathway sugars, and aminosugars. The part concerning oligosaccharides deals with saccharose, trehalose, raffinose, and lactose biosynthesis. The part devoted to sugar alcohols and cyclitols includes the biosynthetic pathways leading to glucitol, inositols, and pseudosaccharides. Extensively used are reaction schemes, sequences, and mechanisms with the enzymes involved and detailed explanations employing sound chemical principles and mechanisms.    

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4

Looijesteijn, Petronella J., Ingeborg C. Boels, Michiel Kleerebezem, and Jeroen Hugenholtz. "Regulation of Exopolysaccharide Production byLactococcus lactis subsp. cremoris by the Sugar Source." Applied and Environmental Microbiology 65, no. 11 (November 1, 1999): 5003–8. http://dx.doi.org/10.1128/aem.65.11.5003-5008.1999.

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ABSTRACT Lactococcus lactis produced more exopolysaccharide (EPS) on glucose than on fructose as the sugar substrate, although the transcription level of the eps gene cluster was independent of the sugar source. A major difference between cells grown on the two substrates was the capacity to produce sugar nucleotides, the EPS precursors. However, the activities of the enzymes required for the synthesis of nucleotide sugars were not changed upon growth on different sugars. The activity of fructosebisphosphatase (FBPase) was by far the lowest of the enzymes involved in precursor formation under all conditions. FBPase catalyzes the conversion of fructose-1,6-diphosphate into fructose-6-phosphate, which is an essential step in the biosynthesis of sugar nucleotides from fructose but not from glucose. By overexpression of the fbp gene, which resulted in increased EPS synthesis on fructose, it was proven that the low activity of FBPase is indeed limiting not only for EPS production but also for growth on fructose as a sugar source.

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5

Cortes, P., F. Dumler, D. L. Paielli, and N. W. Levin. "Glomerular uracil nucleotide synthesis: effects of diabetes and protein intake." American Journal of Physiology-Renal Physiology 255, no. 4 (October 1, 1988): F647—F655. http://dx.doi.org/10.1152/ajprenal.1988.255.4.f647.

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The biosynthesis of uridine 5'-triphosphate (UTP), uridine 5'-diphosphohexoses, and 5'-diphosphohexosamines (UDP-sugars) was studied in isolated rat glomeruli 48 h after streptozotocin-induced diabetes. Compared with control, diabetic glomeruli demonstrated an increase in the following: exogenous orotate utilization, orotate incorporation into UTP and UDP-sugars, UTP accretion rate, and UDP-sugar pool size. Since these phenomena were not associated with enhanced biosynthesis of orotate de novo, the increased glomerular UDP-sugar bioavailability in diabetes is due to enhanced utilization of exogenous orotate. Plasma concentrations of orotate and uridine were measured in control, sham operated, and unilaterally nephrectomized rats receiving 5, 20, or 60% protein diets. The concentration of pyrimidine precursors correlated directly with protein intake, with doubling at the 60% dietary protein level. In conclusion, glomerular uracil ribonucleotide biosynthesis may be modulated by the quantity of dietary protein. Because UDP-sugars are necessary for basement membrane material formation, an increase in their bioavailability may be part of the metabolic change responsible for diabetic glomerulosclerosis. Diets with high protein content could augment this metabolic alteration.

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6

Cambron, L. D., and K. C. Leskawa. "Inhibition of CMP-N-Acetylneuraminic Acid: Lactosylceramide Sialyltransferase by Nucleotides, Nucleotide Sugars and Nucleotide Dialdehydes." Biochemical and Biophysical Research Communications 193, no. 2 (June 1993): 585–90. http://dx.doi.org/10.1006/bbrc.1993.1664.

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7

Dudziak, Gregor, Sven Fey, Lutz Hasbach, and Udo Kragl. "Nanofiltration for Purification of Nucleotide Sugars." Journal of Carbohydrate Chemistry 18, no. 1 (January 1, 1999): 41–49. http://dx.doi.org/10.1080/07328309908543977.

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8

Kleczkowski, Leszek A., and Abir U. Igamberdiev. "Optimization of nucleotide sugar supply for polysaccharide formation via thermodynamic buffering." Biochemical Journal 477, no. 2 (January 22, 2020): 341–56. http://dx.doi.org/10.1042/bcj20190807.

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Plant polysaccharides (cellulose, hemicellulose, pectin, starch) are either direct (i.e. leaf starch) or indirect products of photosynthesis, and they belong to the most abundant organic compounds in nature. Although each of these polymers is made by a specific enzymatic machinery, frequently in different cell locations, details of their synthesis share certain common features. Thus, the production of these polysaccharides is preceded by the formation of nucleotide sugars catalyzed by fully reversible reactions of various enzymes, mostly pyrophosphorylases. These ‘buffering’ enzymes are, generally, quite active and operate close to equilibrium. The nucleotide sugars are then used as substrates for irreversible reactions of various polysaccharide-synthesizing glycosyltransferases (‘engine’ enzymes), e.g. plastidial starch synthases, or plasma membrane-bound cellulose synthase and callose synthase, or ER/Golgi-located variety of glycosyltransferases forming hemicellulose and pectin backbones. Alternatively, the irreversible step might also be provided by a carrier transporting a given immediate precursor across a membrane. Here, we argue that local equilibria, established within metabolic pathways and cycles resulting in polysaccharide production, bring stability to the system via the arrangement of a flexible supply of nucleotide sugars. This metabolic system is itself under control of adenylate kinase and nucleoside-diphosphate kinase, which determine the availability of nucleotides (adenylates, uridylates, guanylates and cytidylates) and Mg2+, the latter serving as a feedback signal from the nucleotide metabolome. Under these conditions, the supply of nucleotide sugars to engine enzymes is stable and constant, and the metabolic process becomes optimized in its load and consumption, making the system steady and self-regulated.

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9

Yang, Ting, and Maor Bar-Peled. "Identification of a novel UDP-sugar pyrophosphorylase with a broad substrate specificity in Trypanosoma cruzi." Biochemical Journal 429, no. 3 (July 14, 2010): 533–43. http://dx.doi.org/10.1042/bj20100238.

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The diverse types of glycoconjugates synthesized by trypanosomatid parasites are unique compared with the host cells. These glycans are required for the parasite survival, invasion or evasion of the host immune system. Synthesis of those glycoconjugates requires a constant supply of nucleotide-sugars (NDP-sugars), yet little is known about how these NDP-sugars are made and supplied. In the present paper, we report a functional gene from Trypanosoma cruzi that encodes a nucleotidyltransferase, which is capable of transforming different types of sugar 1-phosphates and NTP into NDP-sugars. In the forward reaction, the enzyme catalyses the formation of UDP-glucose, UDP-galactose, UDP-xylose and UDP-glucuronic acid, from their respective monosaccharide 1-phosphates in the presence of UTP. The enzyme could also convert glucose 1-phosphate and TTP into TDP-glucose, albeit at lower efficiency. The enzyme requires bivalent ions (Mg2+ or Mn2+) for its activity and is highly active between pH 6.5 and pH 8.0, and at 30–42 °C. The apparent Km values for the forward reaction were 177 μM (glucose 1-phosphate) and 28.4 μM (UTP) respectively. The identification of this unusual parasite enzyme with such broad substrate specificities suggests an alternative pathway that might play an essential role for nucleotide-sugar biosynthesis and for the regulation of the NDP-sugar pool in the parasite.

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10

Pels Rijcken, W. R., B. Overdijk, D. H. van den Eijnden, and W. Ferwerda. "Pyrimidine nucleotide metabolism in rat hepatocytes: evidence for compartmentation of nucleotide pools." Biochemical Journal 293, no. 1 (July 1, 1993): 207–13. http://dx.doi.org/10.1042/bj2930207.

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Pyrimidine nucleotide metabolism in rat hepatocytes was studied by measurement of the labelling kinetics of the various intermediates after double labelling with [14C]orotic acid and [3H]cytidine, the precursors for the de novo and the salvage pathways respectively. For the uridine nucleotides, differences were found for the 14C/3H ratios in the UDP-sugars, in UMP (of RNA) and in their precursor UTP, suggesting the existence of separated flows of the radioactive precursors through the de novo and the salvage pathways. Higher ratios in the UDP-sugars, which are synthesized in the cytoplasm, and a lower ratio in UMP (of RNA) relative to the 14C/3H ratio in UTP indicated that UTP derived from orotic acid is preferentially used for the cytoplasmic biosynthesis of the UDP-sugars. Uridine, derived from cytidine, is preferentially used for the nuclear-localized synthesis of RNA. In contrast to these findings, the 14C/3H ratios in the cytidine derivatives CMP-NeuAc and CMP (of RNA), and in the liponucleotides CDP-choline and CDP-ethanolamine, were all lower than that in the precursor CTP. This indicates a preferential utilization of the salvage-derived CTP for the synthesis of the liponucleotides as well as for RNA and CMP-NeuAc. Similar conclusions could be drawn from experiments in which the intracellular amounts of several uridine- and cytidine-nucleotide-containing derivatives were increased by preincubating the hepatocytes with unlabelled pyrimidine nucleotides or ethanolamine. Based on these data, we propose a refined model for the intracellular compartmentation of pyrimidine nucleotide biosynthesis in which three pools of UTP are distinguished: a pool of de novo-derived molecules and a pool of salvage-derived molecules, both of which are channelled to the site of utilization; in addition an ‘overflow’ pool exists, consisting of molecules having escaped from channelling. An overflow pool could also be distinguished for CTP, but no discrimination between de novo and salvage-derived molecules could be made.

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11

Abeijon, C. "Transporters of nucleotide sugars, nucleotide sulfate and ATP in the Golgi apparatus." Trends in Biochemical Sciences 22, no. 6 (June 1997): 203–7. http://dx.doi.org/10.1016/s0968-0004(97)01053-0.

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12

Ashihara, Hiroshi, Kaori Mitsui, and Toshiko Ukaji. "A Simple Analysis of Purine and Pyrimidine Nucleotides in Plant Cells by High-Performance Liquid Chromatography." Zeitschrift für Naturforschung C 42, no. 3 (March 1, 1987): 297–99. http://dx.doi.org/10.1515/znc-1987-0321.

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Abstract Purine and pyrimidine nucleotides, extracted from cultured plant cells with 6 % perchloric acid, were separated directly with HPLC using anion-exchange Shimpack WAX -1 column. More than fifteen nucleoside mono-, di-, and triphosphates and nucleotide sugars were clearly separated and quantified without any interference from plant phenolic compounds.

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13

Caffaro, Carolina E., Carlos B. Hirschberg, and Patricia M. Berninsone. "Functional Redundancy between Two Caenorhabditis elegans Nucleotide Sugar Transporters with a Novel Transport Mechanism." Journal of Biological Chemistry 282, no. 38 (July 25, 2007): 27970–75. http://dx.doi.org/10.1074/jbc.m704485200.

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Transporters of nucleotide sugars regulate the availability of these substrates required for glycosylation reactions in the lumen of the Golgi apparatus and play an important role in the development of multicellular organisms. Caenorhabditis elegans has seven different sugars in its glycoconjugates, although 18 putative nucleotide sugar transporters are encoded in the genome. Among these, SQV-7, SRF-3, and CO3H5.2 exhibit partially overlapping substrate specificity and expression patterns. We now report evidence of functional redundancy between transporters CO3H5.2 and SRF-3. Reducing the activity of the CO3H5.2 gene product by RNA interference (RNAi) in SRF-3 mutants results in oocyte accumulation and abnormal gonad morphology, whereas comparable RNAi treatment of wild type or RNAi hypersensitive C. elegans strains does not cause detectable defects. We hypothesize this genetic enhancement to be a mechanism to ensure adequate glycoconjugate biosynthesis required for normal tissue development in multicellular organisms. Furthermore, we show that transporters SRF-3 and CO3H5.2, which are closely related in the phylogenetic tree, share a simultaneous and independent substrate transport mechanism that is different from the competitive one previously demonstrated for transporter SQV-7, which shares a lower amino acid sequence identity with CO3H5.2 and SRF-3. Therefore, different mechanisms for transporting multiple nucleotide sugars may have evolved parallel to transporter amino acid divergence.

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14

Nakajima, Kazuki, Emi Ito, Kazuaki Ohtsubo, Ken Shirato, Rina Takamiya, Shinobu Kitazume, Takashi Angata, and Naoyuki Taniguchi. "Mass Isotopomer Analysis of Metabolically Labeled Nucleotide Sugars and N- and O-Glycans for Tracing Nucleotide Sugar Metabolisms." Molecular & Cellular Proteomics 12, no. 9 (May 29, 2013): 2468–80. http://dx.doi.org/10.1074/mcp.m112.027151.

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15

Kleczkowski, Leszek A., and Daniel Decker. "Sugar Activation for Production of Nucleotide Sugars as Substrates for Glycosyltransferases in Plants." Journal of Applied Glycoscience 62, no. 2 (2015): 25–36. http://dx.doi.org/10.5458/jag.jag.jag-2015_003.

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16

BERNINSONE, PATRICIA, and CARLOS B. HIRSCHBERG. "Nucleotide Sugars, Nucleotide Sulfate, and ATP Transporters of the Endoplasmic Reticulum and Golgi Apparatusa,." Annals of the New York Academy of Sciences 842, no. 1 SALIVARY GLAN (April 1998): 91–99. http://dx.doi.org/10.1111/j.1749-6632.1998.tb09636.x.

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17

Kotake, Toshihisa, Chie Hirosawa, Yasutoshi Ando, and Yoichi Tsumuraya. "Generation of nucleotide sugars for biomass formation in plants." Plant Biotechnology 27, no. 3 (2010): 231–36. http://dx.doi.org/10.5511/plantbiotechnology.27.231.

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18

Liu, Jun, Yang Zou, Wanyi Guan, Yafei Zhai, Mengyang Xue, Lan Jin, Xueer Zhao, et al. "Biosynthesis of nucleotide sugars by a promiscuous UDP-sugar pyrophosphorylase from Arabidopsis thaliana (AtUSP)." Bioorganic & Medicinal Chemistry Letters 23, no. 13 (July 2013): 3764–68. http://dx.doi.org/10.1016/j.bmcl.2013.04.090.

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19

Shannon, J. C., F. M. Pien, and K. C. Liu. "Nucleotides and Nucleotide Sugars in Developing Maize Endosperms (Synthesis of ADP-Glucose in brittle-1)." Plant Physiology 110, no. 3 (March 1, 1996): 835–43. http://dx.doi.org/10.1104/pp.110.3.835.

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20

del Val, Ioscani Jimenez, Sarantos Kyriakopoulos, Karen M. Polizzi, and Cleo Kontoravdi. "An optimized method for extraction and quantification of nucleotides and nucleotide sugars from mammalian cells." Analytical Biochemistry 443, no. 2 (December 2013): 172–80. http://dx.doi.org/10.1016/j.ab.2013.09.005.

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21

Zörb, Christian, Dorothee Steinfurth, Victoria Gödde, Karsten Niehaus, and Karl H. Mühling. "Metabolite profiling of wheat flag leaf and grains during grain filling phase as affected by sulfur fertilisation." Functional Plant Biology 39, no. 2 (2012): 156. http://dx.doi.org/10.1071/fp11158.

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Increasing prices for wheat products and fertilisers call for an adjusted agricultural management to maintain yield and to improve product quality. With the increased use of sulfur-free fertilisers in modern cropping systems and the decrease of atmospheric sulfur emissions by industry, sulfur has become a major limiting factor for crop production. The presented data showed that by using GC-MS it was possible to quantitatively detect a set of 72 different metabolites including amino acids, organic acids, sugars, sugar phosphates, and sugar alcohols, phenolic compounds and nucleotides from wheat grains and flag leaves of a pot experiment. A principal component analysis (PCA) revealed a clear separation of flag leaves and grains and a clear separation of non-fertilised and fertilised flag leaves. It could further be shown by PCA, that the low level sulfur fertilisation is also separated from the higher fertilised grains. A considerable influence of the sulfur fertilisation not only on sulfur rich amino acids but also on the sugar metabolism was detected. With increasing sulfur fertilisation six sugars and sugar derivates in the grain such as glucose-6P, galactose, trehalose, cellobiose, melibiose, fumarate, glycerate and the nucleotide uracil were enhanced. Therefore, it was concluded that photosynthesis was limited in developing plants suffering from sulfur deficiency. Late sulfur fertilisation is a procedure that can help to prevent sulfur deficiency. A latent sulfur deficiency at ear emergence can be compensated by late sulfur fertilisation, as wheat plants can replenish sulfate deficits within a short time.

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22

Pels Rijcken, W. R., B. Overdijk, D. H. Van den Eijnden, and W. Ferwerda. "The effect of increasing nucleotide-sugar concentrations on the incorporation of sugars into glycoconjugates in rat hepatocytes." Biochemical Journal 305, no. 3 (February 1, 1995): 865–70. http://dx.doi.org/10.1042/bj3050865.

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Treatment of rat hepatocytes with 0.5 mM concentrations of uridine and cytidine results in increased cellular concentrations of UTP, UDP-sugars and CTP, whereas that of CMP-N-acetylneuraminate remained unchanged [Pels Rijcken, Overdijk, Van den Eijnden and Ferwerda (1993) Biochem. J. 293, 207-213]. The incorporation of radioactivity from 3H-labelled sugars into the cell-associated and secreted glycoconjugate fraction was influenced by these altered cellular concentrations of the nucleotides. For [3H]glucosamine, pretreatment with uridine resulted in a reduction of the glycosylation in both fractions. Increases in the secreted fractions were observed for fucose with both uridine and cytidine and for N-acetylglucosamine with uridine only. With [3H]N-acetylglucosamine, similar specific radioactivities for UDP-N-acetylhexosamine and CMP-N-acetylneuraminate were found, regardless of the pretreatment conditions. With [3H]N-acetylmannosamine, the specific radioactivity of CMP-N-acetylneuraminate showed an almost 2-fold increase on pretreatment. The latter increase did not result in an increased incorporation of radioactivity into the glycoconjugates. It was estimated that, in untreated cells, the ratio of radioactivity incorporated from [3H]glucosamine into glycoconjugate-bound N-acetylhexosamine and N-acetylneuraminate amounted to 2:3. In pretreated cells this ratio changed to approx. 2:1. Overall, the data show that pretreatment resulted in an increased incorporation of N-acetylhexosamine into cell-associated and secreted glycoconjugates, accompanied by a reduction in sialylation. It was concluded that an increased availability of UDP-N-acetylhexosamine caused the increased incorporation of N-acetylhexosamine. The elevated cytosolic level of UDP-N-acetylhexosamine (and of compounds like CMP) is suggested to impair the transport of CMP-acetylneuraminate to the Golgi, resulting in reduced sialylation. This study demonstrates that protein glycosylation can be regulated at the level of the availability of the various nucleotide-sugars in the Golgi lumen.

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23

Hirschberg, Carlos B. "Transporters of nucleotide sugars, nucleotide sulfate and ATP in the Golgi apparatus membrane: Where next?" Glycobiology 7, no. 2 (1997): 169–71. http://dx.doi.org/10.1093/glycob/7.2.169.

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24

Hirschberg, Carlos B., Phillips W. Robbins, and Claudia Abeijon. "TRANSPORTERS OF NUCLEOTIDE SUGARS, ATP, AND NUCLEOTIDE SULFATE IN THE ENDOPLASMIC RETICULUM AND GOLGI APPARATUS." Annual Review of Biochemistry 67, no. 1 (June 1998): 49–69. http://dx.doi.org/10.1146/annurev.biochem.67.1.49.

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25

Wen, Liuqing, Madhusudhan Reddy Gadi, Yuan Zheng, Christopher Gibbons, Shukkoor Muhammed Kondengaden, Jiabin Zhang, and Peng George Wang. "Chemoenzymatic Synthesis of Unnatural Nucleotide Sugars for Enzymatic Bioorthogonal Labeling." ACS Catalysis 8, no. 8 (July 12, 2018): 7659–66. http://dx.doi.org/10.1021/acscatal.8b02081.

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26

ELLING, L. "ChemInform Abstract: Glycobiotechnology: Enzymes for the Synthesis of Nucleotide Sugars." ChemInform 28, no. 34 (August 3, 2010): no. http://dx.doi.org/10.1002/chin.199734347.

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27

Bülter, Thomas, Thomas Schumacher, Darius-Jean Namdjou, Ricardo Gutiérrez Gallego, Henrik Clausen, and Lothar Elling. "Chemoenzymatic Synthesis of Biotinylated Nucleotide Sugars as Substrates for Glycosyltransferases." ChemBioChem 2, no. 12 (December 3, 2001): 884–94. http://dx.doi.org/10.1002/1439-7633(20011203)2:12<884::aid-cbic884>3.0.co;2-2.

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28

Shin, Y. S. "Nucleotide sugars: Determination of cellular levels and discrepancies in results." European Journal of Pediatrics 154, S2 (February 1995): S75—S76. http://dx.doi.org/10.1007/bf02143808.

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29

Xu, Y. K., W. G. Ng, F. R. Kaufman, and G. N. Donnell. "Uridine nucleotide sugars in erythrocytes of patients with galactokinase deficiency." Journal of Inherited Metabolic Disease 12, no. 4 (December 1989): 445–50. http://dx.doi.org/10.1007/bf01802040.

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30

Yang, Ting, Yael Bar-Peled, James Amor Smith, John Glushka, and Maor Bar-Peled. "In-microbe formation of nucleotide sugars in engineered Escherichia coli." Analytical Biochemistry 421, no. 2 (February 2012): 691–98. http://dx.doi.org/10.1016/j.ab.2011.12.028.

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31

Abeijon, C., K. Yanagisawa, EC Mandon, A. Häusler, K. Moremen, CB Hirschberg, and PW Robbins. "Guanosine diphosphatase is required for protein and sphingolipid glycosylation in the Golgi lumen of Saccharomyces cerevisiae." Journal of Cell Biology 122, no. 2 (July 15, 1993): 307–23. http://dx.doi.org/10.1083/jcb.122.2.307.

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Current models for nucleotide sugar use in the Golgi apparatus predict a critical role for the lumenal nucleoside diphosphatase. After transfer of sugars to endogenous macromolecular acceptors, the enzyme converts nucleoside diphosphates to nucleoside monophosphates which in turn exit the Golgi lumen in a coupled antiporter reaction, allowing entry of additional nucleotide sugar from the cytosol. To test this model, we cloned the gene for the S. cerevisiae guanosine diphosphatase and constructed a null mutation. This mutation should reduce the concentrations of GDP-mannose and GMP and increase the concentration of GDP in the Golgi lumen. The alterations should in turn decrease mannosylation of proteins and lipids in this compartment. In fact, we found a partial block in O- and N-glycosylation of proteins such as chitinase and carboxypeptidase Y and underglycosylation of invertase. In addition, mannosylinositolphosphorylceramide levels were drastically reduced.

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32

Standard, Sheila A., Petra Vaux, and Clifford M. Bray. "High-performance liquid chromatography of nucleotides and nucleotide sugars extracted from wheat embryo and vegetable seed." Journal of Chromatography A 318 (January 1985): 433–39. http://dx.doi.org/10.1016/s0021-9673(01)90711-3.

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33

Villiger, Thomas K., Robert F. Steinhoff, Marija Ivarsson, Thomas Solacroup, Matthieu Stettler, Hervé Broly, Jasmin Krismer, et al. "High-throughput profiling of nucleotides and nucleotide sugars to evaluate their impact on antibody N-glycosylation." Journal of Biotechnology 229 (July 2016): 3–12. http://dx.doi.org/10.1016/j.jbiotec.2016.04.039.

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34

MILLA, M., J. CAPASSO, and C. B. HIRSCHBERG. "Translocation of nucleotide sugars and nucleotide sulphate across membranes of the endoplasmic reticulum and Golgi apparatus." Biochemical Society Transactions 17, no. 3 (June 1, 1989): 447–48. http://dx.doi.org/10.1042/bst0170447.

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35

RANCOUR, David M., and Anant K. MENON. "Identification of endoplasmic reticulum proteins involved in glycan assembly: synthesis and characterization of P3-(4-azidoanilido)uridine 5′-triphosphate, a membrane-topological photoaffinity probe for uridine diphosphate-sugar binding proteins." Biochemical Journal 333, no. 3 (August 1, 1998): 661–69. http://dx.doi.org/10.1042/bj3330661.

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Much of the enzymic machinery required for the assembly of cell surface carbohydrates is located in the endoplasmic reticulum (ER) of eukaryotic cells. Structural information on these proteins is limited and the identity of the active polypeptide(s) is generally unknown. This paper describes the synthesis and characteristics of a photoaffinity reagent that can be used to identify and analyse members of the ER glycan assembly apparatus, specifically those glycosyltransferases, nucleotide phosphatases and nucleotide–sugar transporters that recognize uridine nucleotides or UDP-sugars. The photoaffinity reagent, P3-(4-azidoanilido)uridine 5´-triphosphate (AAUTP), was synthesized easily from commercially available precursors. AAUTP inhibited the activity of ER glycosyltransferases that utilize UDP-GlcNAc and UDP-Glc, indicating that it is recognized by UDP-sugar-binding proteins. In preliminary tests AAUTP[α-32P] labelled bovine milk galactosyltransferase, a model UDP-sugar-utilizing enzyme, in a UV-light-dependent, competitive and saturable manner. When incubated with rat liver ER vesicles, AAUTP[α-32P] labelled a discrete subset of ER proteins; labelling was light-dependent and metal ion-specific. Photolabelling of intact ER vesicles with AAUTP[α-32P] caused selective incorporation of radioactivity into proteins with cytoplasmically disposed binding sites; UDP-Glc:glycoprotein glucosyltransferase, a lumenal protein, was labelled only when the vesicle membrane was disrupted. These data indicate that AAUTP is a membrane topological probe of catalytic sites in target proteins. Strategies for using AAUTP to identify and study novel ER proteins involved in glycan assembly are discussed.

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Garzon, Catalina Duran, Michelle Lequart, Carsten Rautengarten, Solène Bassard, Hélène Sellier-Richard, Pierre Baldet, Joshua L. Heazlewood, et al. "Regulation of carbon metabolism in two maize sister lines contrasted for chilling tolerance." Journal of Experimental Botany 71, no. 1 (September 26, 2019): 356–69. http://dx.doi.org/10.1093/jxb/erz421.

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Parker, L. L., and B. G. Hall. "Characterization and nucleotide sequence of the cryptic cel operon of Escherichia coli K12." Genetics 124, no. 3 (March 1, 1990): 455–71. http://dx.doi.org/10.1093/genetics/124.3.455.

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Abstract Wild-type Escherichia coli are not able to utilize beta-glucoside sugars because the genes for utilization of these sugars are cryptic. Spontaneous mutations in the cel operon allow its expression and enable the organism to ferment cellobiose, arbutin and salicin. In this report we describe the structure and nucleotide sequence of the cel operon. The cel operon consists of five genes: celA, whose function is unknown; celB and celC which encode phosphoenolpyruvate-dependent phosphotransferase system enzyme IIcel and enzyme IIIcel, respectively, for the transport and phosphorylation of beta-glucoside sugars; celD, which encodes a negative regulatory protein; and celF, which encodes a phospho-beta-glucosidase that acts on phosphorylated cellobiose, arbutin and salicin. The mutationally activated cel operon is induced in the presence of its substrates, and is repressed in their absence. A comparison of proteins encoded by the cel operon with functionally equivalent proteins of the bgl operon, another cryptic E. coli gene system responsible for the catabolism of beta-glucoside sugars, revealed no significant homology between these two systems despite common functional characteristics. The celD and celF encoded repressor and phospho-beta-glucosidase proteins are homologous to the melibiose regulatory protein and to the melA encoded alpha-galactosidase of E. coli, respectively. Furthermore, the celC encoded PEP-dependent phosphotransferase system enzyme IIIcel is strikingly homologous to an enzyme IIIlac of the Gram-positive organism Staphylococcus aureus. We conclude that the genes for these two enzyme IIIs diverged much more recently than did their hosts, indicating that E. coli and S. aureus have undergone relatively recent exchange of chromosomal genes.

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Nakajima, Kazuki, Shinobu Kitazume, Takashi Angata, Reiko Fujinawa, Kazuaki Ohtsubo, Eiji Miyoshi, and Naoyuki Taniguchi. "Simultaneous determination of nucleotide sugars with ion-pair reversed-phase HPLC." Glycobiology 20, no. 7 (April 5, 2010): 865–71. http://dx.doi.org/10.1093/glycob/cwq044.

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Gibeaut, David M. "Nucleotide sugars and glycosyltransferases for synthesis of cell wall matrix polysaccharides." Plant Physiology and Biochemistry 38, no. 1-2 (January 2000): 69–80. http://dx.doi.org/10.1016/s0981-9428(00)00167-4.

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Elling, Lothar. "ChemInform Abstract: Enzymatic Tools for the Synthesis of Nucleotide (Deoxy)sugars." ChemInform 31, no. 44 (October 31, 2000): no. http://dx.doi.org/10.1002/chin.200044280.

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Ikeda, Kiyoshi, Yoshihiro Nagao, and Kazuo Achiwa. "Synthesis of sialic acid-containing nucleotide sugars: CMP-sialic acid analogs." Carbohydrate Research 224 (February 1992): 123–31. http://dx.doi.org/10.1016/0008-6215(92)84099-e.

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Feng, Hua-Tao, Niki Wong, Sheena Wee, and May May Lee. "Simultaneous determination of 19 intracellular nucleotides and nucleotide sugars in Chinese Hamster ovary cells by capillary electrophoresis." Journal of Chromatography B 870, no. 1 (July 2008): 131–34. http://dx.doi.org/10.1016/j.jchromb.2008.05.038.

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43

Hothersall, J. S., R. P. Muirhead, C. E. Taylaur, S. Kunjara, and P. Mclean. "Changes in Uridine Nucleotides and Uridine Nucleotide Sugars in Diabetic Rat Lens: Implications in Membrane Glycoprotein Formation." Biochemical Medicine and Metabolic Biology 50, no. 3 (December 1993): 292–300. http://dx.doi.org/10.1006/bmmb.1993.1071.

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44

Niemann, Michael C. E., Isabel Bartrina, Angel Ashikov, Henriette Weber, Ondřej Novák, Lukáš Spíchal, Miroslav Strnad, et al. "Arabidopsis ROCK1 transports UDP-GlcNAc/UDP-GalNAc and regulates ER protein quality control and cytokinin activity." Proceedings of the National Academy of Sciences 112, no. 1 (December 22, 2014): 291–96. http://dx.doi.org/10.1073/pnas.1419050112.

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The formation of glycoconjugates depends on nucleotide sugars, which serve as donor substrates for glycosyltransferases in the lumen of Golgi vesicles and the endoplasmic reticulum (ER). Import of nucleotide sugars from the cytosol is an important prerequisite for these reactions and is mediated by nucleotide sugar transporters. Here, we report the identification of REPRESSOR OF CYTOKININ DEFICIENCY 1 (ROCK1, At5g65000) as an ER-localized facilitator of UDP-N-acetylglucosamine (UDP-GlcNAc) and UDP-N-acetylgalactosamine (UDP-GalNAc) transport in Arabidopsis thaliana. Mutant alleles of ROCK1 suppress phenotypes inferred by a reduced concentration of the plant hormone cytokinin. This suppression is caused by the loss of activity of cytokinin-degrading enzymes, cytokinin oxidases/dehydrogenases (CKXs). Cytokinin plays an essential role in regulating shoot apical meristem (SAM) activity and shoot architecture. We show that rock1 enhances SAM activity and organ formation rate, demonstrating an important role of ROCK1 in regulating the cytokinin signal in the meristematic cells through modulating activity of CKX proteins. Intriguingly, genetic and molecular analysis indicated that N-glycosylation of CKX1 was not affected by the lack of ROCK1-mediated supply of UDP-GlcNAc. In contrast, we show that CKX1 stability is regulated in a proteasome-dependent manner and that ROCK1 regulates the CKX1 level. The increased unfolded protein response in rock1 plants and suppression of phenotypes caused by the defective brassinosteroid receptor bri1-9 strongly suggest that the ROCK1 activity is an important part of the ER quality control system, which determines the fate of aberrant proteins in the secretory pathway.

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Freitas, Rui, Marta Relvas-Santos, Rita Azevedo, Janine Soares, Elisabete Fernandes, Beatriz Teixeira, Lúcio Lara Santos, André M. N. Silva, and José Alexandre Ferreira. "Single-pot enzymatic synthesis of cancer-associated MUC16 O-glycopeptide libraries and multivalent protein glycoconjugates: a step towards cancer glycovaccines." New Journal of Chemistry 45, no. 20 (2021): 9197–211. http://dx.doi.org/10.1039/d0nj06021f.

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Glycosyltransferases and nucleotide sugars are combined in single-pot settings to synthesize a library of cancer-associated MUC16 O-glycopeptides and multivalent protein glycoconjugates foreseeing future development of cancer glycovaccines.

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Fletcher, M. H., C. E. Burns-Lynch, K. W. Knouse, L. T. Abraham, C. W. DeBrosse, and W. M. Wuest. "A novel application of the Staudinger ligation to access neutral cyclic di-nucleotide analog precursors via a divergent method." RSC Advances 7, no. 47 (2017): 29835–38. http://dx.doi.org/10.1039/c7ra06045a.

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Herein we present a scalable and divergent synthesis of cyclic di-nucleotide analog precursors facilitated by differentiated di-amino sugars and a Staudinger ligation to provide medium-sized macrocycles featuring carbamate or urea linkages.

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Sampaio Guther, Maria Lucia, Alan R. Prescott, Sabine Kuettel, Michele Tinti, and Michael A. J. Ferguson. "Nucleotide sugar biosynthesis occurs in the glycosomes of procyclic and bloodstream form Trypanosoma brucei." PLOS Neglected Tropical Diseases 15, no. 2 (February 16, 2021): e0009132. http://dx.doi.org/10.1371/journal.pntd.0009132.

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In Trypanosoma brucei, there are fourteen enzymatic biotransformations that collectively convert glucose into five essential nucleotide sugars: UDP-Glc, UDP-Gal, UDP-GlcNAc, GDP-Man and GDP-Fuc. These biotransformations are catalyzed by thirteen discrete enzymes, five of which possess putative peroxisome targeting sequences. Published experimental analyses using immunofluorescence microscopy and/or digitonin latency and/or subcellular fractionation and/or organelle proteomics have localized eight and six of these enzymes to the glycosomes of bloodstream form and procyclic form T. brucei, respectively. Here we increase these glycosome localizations to eleven in both lifecycle stages while noting that one, phospho-N-acetylglucosamine mutase, also localizes to the cytoplasm. In the course of these studies, the heterogeneity of glycosome contents was also noted. These data suggest that, unlike other eukaryotes, all of nucleotide sugar biosynthesis in T. brucei is compartmentalized to the glycosomes in both lifecycle stages. The implications are discussed.

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Tokuda, Masahiro, Masugu Kamei, Seiko Yui, and Fumihiro Koyama. "Rapid resolution of nucleotide sugars by lectin affinity high-performance liquid chromatography." Journal of Chromatography A 323, no. 2 (January 1985): 434–38. http://dx.doi.org/10.1016/s0021-9673(01)90409-1.

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Buelter, Thomas, Thomas Schumacher, Darius-Jean Namdjou, Ricardo Gutierrez Gallego, Henrik Clausen, and Lothar Elling. "ChemInform Abstract: Chemoenzymatic Synthesis of Biotinylated Nucleotide Sugars as Substrates for Glycosyltransferases." ChemInform 33, no. 15 (May 22, 2010): no. http://dx.doi.org/10.1002/chin.200215208.

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Zervosen, Astrid, Andreas Stein, Holger Adrian, and Lothar Elling. "Combined enzymatic synthesis of nucleotide (deoxy) sugars from sucrose and nucleoside monophosphates." Tetrahedron 52, no. 7 (February 1996): 2395–404. http://dx.doi.org/10.1016/0040-4020(95)01081-5.

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